David Rakoff’s Last Deadline

Love’s Labors, Published

David Rakoff’s third book of essays, “Half Empty,” came out in the fall of 2010, nine months after he learned that the pain he’d been experiencing in his left arm and shoulder was the result of a malignant sarcoma. David was an extraordinary essayist — the book won the Thurber Prize for American Humor, and, like his two previous collections, was a best seller — so it came as some surprise when he called his editor at Doubleday to say that he wanted his next book to be a novel written in rhyme.

“I will admit I paused for a very long time,” Bill Thomas, the editor, said recently. “A novel in verse. But David was extremely passionate about the project. He’d been ruminating on it for a decade. This was late 2010, and of course he was quite sick at this point; he’d been battling cancer for some time. But with a writer of David’s caliber, who I personally loved and admired very much, I just said, ‘O.K., we’ll figure out a way to publish it.’ ”

For the next year and a half, David wrote, between surgeries and chemotherapy regimens and in the face of the growing awareness that his cancer, as he put it, “would not be denied.” The process of writing had always been an exercise in anguish management for him (he once said in an interview that writing was like having his teeth pulled out — through his penis), but to me and other friends, this book seemed different. He discussed the fate of his characters, he read passages to visitors from his bed, he sent e-mails saying he was feeling good because the writing had gone well that day.

The last time I had dinner with David, about six weeks before he died, he was so weak that it was impossible to imagine him mustering the strength to work. But he was so close, he said. “I need to finish it, and then I’ll be ready.”

A week later, the book was done. “He rang me up and said, ‘The good news is, I have actually finished before my deadline’ — which is an unusual call to get from an author,” Mr. Thomas said. “And then he said, ‘The bad news is, you’ll be publishing it posthumously.’ I read the manuscript and knew right away it was something exceptional. He poured his — I mean this literally — he poured his life into it: his ideas, his thoughts, his wit, his graciousness, his sense of tragedy. And he mastered this very difficult form.”

Ira Glass, a longtime friend of David’s and the executive producer of the radio show “This American Life,” said of the book: “Its dirty little secret is that David was probably a better novelist than he was an essayist. I mean, he was a great essayist, famous and all that, but that came so hard to him, and I think writing this, writing drama, gave him so much more pleasure.”

Over a series of meetings in David’s apartment, he and Mr. Thomas began to plan the publication of “Love, Dishonor, Marry, Die, Cherish, Perish,” which will be released on July 16, less than a year since his death last August at the age of 47. The story spans decades, from turn-of-the-20th-century Chicago to midcentury Manhattan to San Francisco at the height of the AIDS crisis, and then to the near-present, when a grief-stricken man opens a wrapped box from long ago, and all the years — with the longings and indignities and small, eventful generosities they contain — collapse into a single moment.

David wrote with biting wit about the inevitability of death and the futility of positive thinking — the “warning” sticker on “Half Empty” reads: “No inspirational life lessons will be found here” — but he lived a remarkably inspired life. In addition to being an essayist, he was an actor and playwright and screenwriter (the short film that he adapted and appeared in, “The New Tenants,” won an Academy Award); he was a frequent and wildly popular contributor to “This American Life”; and as the many friends to whom he gave drawings and woodcuts and hand-painted boxes and tiny sculptures can attest, he was an extraordinary visual artist.

He was extreme in both his generosity and his self-sufficiency; to be his friend meant to reckon with what felt like an imbalance in kindness. For the small circle of friends involved in the project of publishing his novel, this quality of David’s only intensified their sense of urgency and their desire to bring it into the world — to a wider circle of readers who didn’t know him — in a way that David would have wanted.

“What is so special to me about the book,” Mr. Thomas said, “is that it is the purest distillation of David’s belief that we live in a world that is essentially cruel and indifferent, but there are remedies for that. And the remedies are kindness and beauty. It’s very clever and erudite, and it’s very, very funny, as David was, but fundamentally it is a brief for kindness.

“I told him that this was the best thing he’d ever written,” he continued. “David was his own worst critic to a fault, but he said, ‘I know it is.’ Which was not like him.”

To oversee the design of the book, Mr. Thomas turned to Chip Kidd, a longtime friend of David’s who designed his first book, 2001’s “Fraud.” “It was a matter of maybe two weeks at that point,” Mr. Kidd said of David’s worsening condition. “We were all working through tears. I just tried to focus on doing the best job I could and not think of its being posthumous. I wanted the book to look alive, because the writing is so alive.”

David had wanted to do the illustrations himself, Mr. Kidd said, “but he was too weak at that point, and we were racing against time.” Mr. Kidd suggested that the artist Seth — a fellow Canadian and fellow romantic who had recently drawn the cover for “The Portable Dorothy Parker” — had the perfect sensibility for the novel, and David agreed.

What Mr. Kidd imagined for the cover was an illustration of the red-haired woman who is central to all that unfurls in the novel, with die-cut holes that reveal the title beneath them. There’s a layering effect that echoes, in the object itself, the way that years and lives and incidents in the story are layered upon one another, the present carrying the past within it. When you open the cover there is, as Mr. Kidd put it, “this swirl of letters, like a word search,” that captures both the lushness of David’s poetry and the idea that there are secrets in the book hiding in plain sight.

Mr. Kidd made the prototypes by hand, cutting each hole with an X-acto knife, “which maybe sounds weird and martyrish,” he said, “but I knew that’s how David would have done it.”

In those final weeks, Mr. Thomas said, they worked out the format and design with David. “Typically I would show up at his apartment, and he would have prepared cookies for my kids, though his illness was progressing and he was getting weaker and weaker. As you can imagine, those were emotional conversations. And then somehow, miraculously, he was also able to do the audio.”

David died late in the evening on Aug. 9. Over the course of the last week of July, he recorded the audiobook with Ira in the studio of “This American Life.”

“He made clear that he wanted to read it himself,” Ira said. “He had such tremendous facility as a reader and actor — he’s one of the greatest performers we’ve ever had on the show — and I think he just heard it in his head and knew how he wanted it to sound.”

They did four two-hour sessions, the last one on Saturday, July 28. “We talked about putting the last one off until the following week, but he wasn’t sure he’d be healthy enough,” Ira said. I brought David to that last session. In the elevator on the way up to the studio, he fell against me and closed his eyes, and when we got inside, he lay down on the couch. Ira made tea for him, and eventually David sat up and said he was ready. They went into the recording booth, and David was transformed. His breathing was labored, and he was interrupted every few words by horrible coughing fits, but, as Ira put it: “He performed the hell out of it. Even though at that point he had a voice like a broken-down car.”

For weeks after they recorded, Ira went through and, where possible, digitally removed David’s labored breaths and replaced them with pauses. “It was really one of the most simultaneously tedious and mournful things I’ve ever done,” he said. “Those two things aren’t often combined. It was just so compulsive as an act. It was like building a casket for someone you love out of tiny mosaic tiles.”

I found it beautiful and heartbreaking to listen to the audio files. At one point, David reads a passage about a gay artist, Cliff, who is dying of AIDS:

It was sadness that gripped him, far more than the fear

That, if facing the truth, he had maybe a year.

When poetic phrases like “eyes, look your last”

Become true, all you want is to stay, to hold fast.

A new, fierce attachment to all of this world

Now pierced him, it stabbed like a deity-hurled

Lightning bolt lancing him, sent from above.

Left him giddy and tearful. It felt like young love.

He’d thought of himself as uniquely proficient

At seeing, but now that sense felt insufficient.

He wanted to grab, to possess, to devour

To eat with his eyes, how he needed that power.

In one of his last public appearances, in May 2012, at a live show of “This American Life,” David performed a dance that was choreographed by Monica Bill Barnes & Company. He had first seen the company that spring, with Ira and his wife, Anaheed Alani. In a break from recording, he explained to Ira that he wrote this passage immediately afterward, to capture the feeling he had of knowing you have just a few months left to exist in the world.

To suggest that the book is death-obsessed, though, would be to miss what’s so delightful about it, that it’s hilarious and lewd and shot through with a longing for life. There’s a remarkable, self-mocking passage in which a character named Mindy gets up to give a toast at her sister’s wedding. Her trademark, she explains to the crowd, is giving toasts in rhyming verse.

“Hello, I am Mindy, and this is my speech.

Susan, you are the best sister plus you’ve always had great comic timing.

So I know you won’t hold it against me when I do my specialty

and

make my toast in rhyming.”

On the audio, David slips into character and reads Mindy’s poem with a thick Long Island accent; on the edited tape you can hear Ira laughing in the background.

“But listen to this,” Ira said when he played it for me. “Let me turn my part down so you can hear what he says.”

David’s voice is thin and weak, but so clearly pleased. “It might be my favorite part,” David says. I wanted to listen to that moment over and over, the sound of him knowing he’d achieved something even he couldn’t deny.